Crystal structure, Hirshfeld surface and crystal void analysis, intermolecular interaction energies, DFT calculations and energy frameworks of 2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide


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Irrou E., Elmachkouri Y. A., Mazzah A., HÖKELEK T., Haoudi A., Mague J. T., ...More

Acta Crystallographica Section E: Crystallographic Communications, vol.79, no.Pt 11, pp.1037-1043, 2023 (ESCI) identifier identifier

Abstract

In the title molecule, C8H7NO3S, the nitrogen atom has a planar environment, and the thiazine ring exhibits a screw-boat conformation. In the crystal, corrugated layers of molecules parallel to the ab plane are formed by N-H O and C-H O hydrogen bonds together with C-H π(ring) and S O π(ring) interactions. The layers are connected by additional C-H O hydrogen bonds and π-stacking interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H O/O H (49.4%), H H (23.0%) and H C/C H (14.1%) interactions. The volume of the crystal voids and the percentage of free space were calculated as 75.4 Å 3 and 9.3%. Density functional theory (DFT) computations revealed N-H O and C-H O hydrogen-bonding energies of 43.3, 34.7 and 34.4 kJ mol- 1, respectively. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via the electrostatic energy contribution. Moreover, the DFT-optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.